메뉴 건너뛰기




Volumn 36, Issue 20, 1993, Pages 2964-2972

Imidazol-1-yl and Pyridin-3-yl Derivatives of 4-Phenyl-1,4-dihydropyridines Combining Ca2+ Antagonism and Thromboxane A2 Synthase Inhibition

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDRO 4 [3 (1H IMIDAZOL 1 YL)PHENYL] 2,6 DIMETHYL 3,5 PYRIDINEDICARBOXYLIC ACID DIETHYL ESTER; CALCIUM ANTAGONIST; DIHYDROPYRIDINE DERIVATIVE; FCE 24265; NIFEDIPINE; THROMBOXANE SYNTHASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 0027428755     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00072a017     Document Type: Article
Times cited : (122)

References (46)
  • 1
    • 0025873758 scopus 로고
    • Calcium antagonists: An Overview
    • and references cited therein
    • Hansson, L. Calcium antagonists: An Overview. Am. Heart J. 1991, 122, 308–311 and references cited therein.
    • (1991) Am. Heart J. , vol.122 , pp. 308-311
    • Hansson, L.1
  • 3
    • 0023801196 scopus 로고
    • Therapeutic trial of intravenous nimodipine in patients with established cerebral vasospasm after rupture of intracranial aneurysm
    • Buchbeit, J. M.; Tremoulet, M. Therapeutic trial of intravenous nimodipine in patients with established cerebral vasospasm after rupture of intracranial aneurysm. Neurosurg. 1988, 23, 164-157.
    • (1988) Neurosurg. , vol.23
    • Buchbeit, J.M.1    Tremoulet, M.2
  • 4
    • 0021843304 scopus 로고
    • Complexity of enzyme release during acute myocardial infarction in a controlled study with early nifedipine treatment
    • Loogna, E.; Sylven, C.; Groth, T.; Mogensen, L. Complexity of enzyme release during acute myocardial infarction in a controlled study with early nifedipine treatment. Eur. Heart J. 1985, 6, 114–119.
    • (1985) Eur. Heart J. , vol.6 , pp. 114-119
    • Loogna, E.1    Sylven, C.2    Groth, T.3    Mogensen, L.4
  • 5
    • 0000408340 scopus 로고
    • The secondary prevention re-infarction Israeli nifedipine trial (SPRINT) II: design and methods, results
    • SPRINT Study Group. The secondary prevention re-infarction Israeli nifedipine trial (SPRINT) II: design and methods, results. Eur. Heart. J. 1988, 9 (Suppl. I), 350A.
    • (1988) Eur. Heart. J. , vol.9 , pp. 350A
  • 6
    • 0018709215 scopus 로고
    • Myocardial Infarction Study Group. Secondary prevention of ischemic heart disease: a long term controlled lidoflazine study
    • Myocardial Infarction Study Group. Secondary prevention of ischemic heart disease: a long term controlled lidoflazine study. Acta Cardiol. 1979, 34 (Suppl. 24), 7–46.
    • (1979) Acta Cardiol. , vol.34 , pp. 7-46
  • 7
    • 85022254366 scopus 로고
    • Calcium Antagonists in Chronic Stable Angina Pectoris
    • Subramanian, V. B. Calcium Antagonists in Chronic Stable Angina Pectoris. Excerpta Medica (Amsterdam) 1983, 97–116.
    • (1983) Excerpta Medica (Amsterdam) , pp. 97-116
    • Subramanian, V.B.1
  • 8
    • 0019838831 scopus 로고
    • Interim report of multicenter double-blind, placebo controlled studies of nifedipine in chronic stable angina
    • Mueller, H. S.; Chahine, R. A. Interim report of multicenter double-blind, placebo controlled studies of nifedipine in chronic stable angina. Am. J. Med. 1981, 71, 646–657.
    • (1981) Am. J. Med. , vol.71 , pp. 646-657
    • Mueller, H.S.1    Chahine, R.A.2
  • 10
    • 0020066942 scopus 로고
    • Randomized double-blind comparison of nifedipine and isosorbide dinitrate therapy in variant angina pectoris due to coronary artery spasm
    • Ginsburg, R.; Lamb, I. H.; Schroeder, J. S.; Harrison, M. H.; Harrison, D. C. Randomized double-blind comparison of nifedipine and isosorbide dinitrate therapy in variant angina pectoris due to coronary artery spasm. Am. Heart. J. 1982, 103, 44–48.
    • (1982) Am. Heart. J. , vol.103 , pp. 44-48
    • Ginsburg, R.1    Lamb, I.H.2    Schroeder, J.S.3    Harrison, M.H.4    Harrison, D.C.5
  • 11
    • 0024460849 scopus 로고
    • Calcium channel blockers in acute myocardial infarction and unstable angina: an overview
    • Held, P. H.; Yusuf, S.; Furberg, C. D. Calcium channel blockers in acute myocardial infarction and unstable angina: an overview. Br. Med. J. 1989, 299, 1187.
    • (1989) Br. Med. J. , vol.299 , pp. 1187
    • Held, P.H.1    Yusuf, S.2    Furberg, C.D.3
  • 12
    • 0025946622 scopus 로고
    • Calcium Antagonists in Patients with Heart Failure
    • Reicher-Reiss, H.; Barasch, E. Calcium Antagonists in Patients with Heart Failure. Drugs 1991, 42(3), 343–364.
    • (1991) Drugs , vol.42 , Issue.3 , pp. 343-364
    • Reicher-Reiss, H.1    Barasch, E.2
  • 13
    • 0025602265 scopus 로고
    • Effect of nimodipine on acute ischemic stroke: pooled results from five randomized trials
    • Gelmers, H. J.; Henneric, N. Effect of nimodipine on acute ischemic stroke: pooled results from five randomized trials. Stroke 1990, 21 (Suppl. IV), 81-IV84.
    • (1990) Stroke , vol.21 , pp. 81-IV84
    • Gelmers, H.J.1    Henneric, N.2
  • 15
    • 0025845395 scopus 로고
    • Calcium Antagonists and Atherosclerosis
    • and references cited therein
    • Triggle, D. J. Calcium Antagonists and Atherosclerosis. Drugs Today 1991, 27(3), 147–155 and references cited therein.
    • (1991) Drugs Today , vol.27 , Issue.3 , pp. 147-155
    • Triggle, D.J.1
  • 16
    • 0021969362 scopus 로고
    • “In vivo” production of Thromboxane in acute human myocardial infarction: a preliminary study
    • Vesterqvist, O.; Edhag, O.; Green, K.; Henriksson, P. “In vivo” production of Thromboxane in acute human myocardial infarction: a preliminary study. Thrombosis Res. 1985, 37, 459–464.
    • (1985) Thrombosis Res. , vol.37 , pp. 459-464
    • Vesterqvist, O.1    Edhag, O.2    Green, K.3    Henriksson, P.4
  • 18
    • 0026625771 scopus 로고
    • Thromboxane synthesis and action within the kidney
    • Remuzzi, G.; FitzGerald, G. A.; Patrono, C. Thromboxane synthesis and action within the kidney. Kidney Int. 1992, 41, 1483–1493.
    • (1992) Kidney Int. , vol.41 , pp. 1483-1493
    • Remuzzi, G.1    FitzGerald, G.A.2    Patrono, C.3
  • 20
    • 0023024261 scopus 로고
    • Effecte of thromboxane synthetase inhibitor (OKY-046) and a lipoxygenase inhibitor (AA-861) on bronchial responsiveness to acetylcholine in asthmatic subjects
    • Fujimura, M.; Sasaki, F.; Nakatsumi, Y.; Takahashi, Y.; Hifumi, S.; Taga, K.; Mifune, J.; Tanaka, T.; Matsuda, T. Effecte of thromboxane synthetase inhibitor (OKY-046) and a lipoxygenase inhibitor (AA-861) on bronchial responsiveness to acetylcholine in asthmatic subjects. Thorax 1986, 41, 955–959.
    • (1986) Thorax , vol.41 , pp. 955-959
    • Fujimura, M.1    Sasaki, F.2    Nakatsumi, Y.3    Takahashi, Y.4    Hifumi, S.5    Taga, K.6    Mifune, J.7    Tanaka, T.8    Matsuda, T.9
  • 21
    • 0024406069 scopus 로고
    • Clinical study of OKY-046, a thromboxane synthetase inhibitor, in prevention of cerebral vasospasms and delayed cerebral ischaemic symptoms after subarachnoid haemorrhage due to aneurysmal rupture: a randomized double-blind study
    • Suzuki, S.; Sano, K.; Handa, H.; Asano, T.; Tamura, A.; Yonekawa, Y.; Ono, H.; Tachibana, N.; Hanaoka, K. Clinical study of OKY-046, a thromboxane synthetase inhibitor, in prevention of cerebral vasospasms and delayed cerebral ischaemic symptoms after subarachnoid haemorrhage due to aneurysmal rupture: a randomized double-blind study. Neurol. Res. 1989, 11, 79–88.
    • (1989) Neurol. Res. , vol.11 , pp. 79-88
    • Suzuki, S.1    Sano, K.2    Handa, H.3    Asano, T.4    Tamura, A.5    Yonekawa, Y.6    Ono, H.7    Tachibana, N.8    Hanaoka, K.9
  • 22
    • 85007976017 scopus 로고
    • Clinical effects of a thromboxane synthetase inhibitor (OKY-046) on diabetic patients: effects of renal function
    • Sakamoto, N., Albert, K. G. M. M., Motta, N., Eds.; Elsevier (Biomedical Division): New York
    • Ono, Y.; Misawa, K.; Kudoh, M.; Nakagawa, S. Clinical effects of a thromboxane synthetase inhibitor (OKY-046) on diabetic patients: effects of renal function. In Recent Trends in management of diabetes mellitus; Sakamoto, N., Albert, K. G. M. M., Motta, N., Eds.; Elsevier (Biomedical Division): New York, 1987; pp 546–548.
    • (1987) Recent Trends in management of diabetes mellitus , pp. 546-548
    • Ono, Y.1    Misawa, K.2    Kudoh, M.3    Nakagawa, S.4
  • 26
    • 0024477866 scopus 로고
    • 2+ Channel Ligands: Structure-Function Relationships of The 1,4-Dihydropyridines
    • 2+ Channel Ligands: Structure-Function Relationships of The 1,4-Dihydropyridines. Med. Res. Rev. 1989, 9 (2), 123–180.
    • (1989) Med. Res. Rev. , vol.9 , Issue.2 , pp. 123-180
    • Triggle, D.J.1    Langs, D.A.2    Janis, R.A.3
  • 27
    • 0004390903 scopus 로고
    • 2 Antagonists
    • and references therein
    • 2 Antagonists. Curr. Opin. Ther. Pat. 1991, 1(9), 1343–1373 and references therein.
    • (1991) Curr. Opin. Ther. Pat. , vol.1 , Issue.9 , pp. 1343-1373
    • Cozzi, P.1    Salvati, P.2
  • 28
    • 0021909254 scopus 로고
    • Thromboxane synthetase inhibitors (TXSI). Design, synthesis, and evaluation of a novel series of ω-pyridiylalkenoic acids
    • Kato, K.; Ohkawa, S.; Terao, S.; Terashita, Z.; Nishikawa, K. Thromboxane synthetase inhibitors (TXSI). Design, synthesis, and evaluation of a novel series of ω-pyridiylalkenoic acids. J. Med. Chem. 1985, 28, 287–294.
    • (1985) J. Med. Chem. , vol.28 , pp. 287-294
    • Kato, K.1    Ohkawa, S.2    Terao, S.3    Terashita, Z.4    Nishikawa, K.5
  • 30
    • 85078025609 scopus 로고
    • Methods for the Preparation of Acetals from Alcohols or Oxiranes and Carbonyl Compounds
    • Meskens, F. A. J. Methods for the Preparation of Acetals from Alcohols or Oxiranes and Carbonyl Compounds. Synthesis 1981, 501.
    • (1981) Synthesis , pp. 501
    • Meskens, F.A.J.1
  • 31
    • 0023212166 scopus 로고
    • Cardiotonic Agents. 5. 1,2-Dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-6-methyl-2-oxo-3-pyridine-carbonitriles and Related Compounds. Synthesis and Inotropic Activity
    • Sircar, I.; Duell, B. L.; Bristol, A.; Weishaar, R. E.; Evans, D. B. Cardiotonic Agents. 5. 1,2-Dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-6-methyl-2-oxo-3-pyridine-carbonitriles and Related Compounds. Synthesis and Inotropic Activity. J. Med. Chem. 1987, 30, 1023–1029.
    • (1987) J. Med. Chem. , vol.30 , pp. 1023-1029
    • Sircar, I.1    Duell, B.L.2    Bristol, A.3    Weishaar, R.E.4    Evans, D.B.5
  • 33
    • 85038545187 scopus 로고
    • Chem. Abstr. 1966, 65, 13686a.
    • (1966) Chem. Abstr. , vol.65 , pp. 13686a
  • 34
    • 85022240579 scopus 로고
    • EP 34577 A2
    • Eisai Co. EP 34577 A2, 1989.
    • (1989)
  • 36
    • 0019620802 scopus 로고
    • 4-Aryldihydropyridines, a New Class of Highly Active Calcium Antagonists
    • Bossert, F.; Meyer, H.; Wehinger, E. 4-Aryldihydropyridines, a New Class of Highly Active Calcium Antagonists. Angew. Chem., Int. Ed. Engl. 1981, 20, 762–784.
    • (1981) Angew. Chem., Int. Ed. Engl. , vol.20 , pp. 762-784
    • Bossert, F.1    Meyer, H.2    Wehinger, E.3
  • 37
    • 0020058582 scopus 로고
    • Crystal Structures and Pharmacological Activity of Calcium Channel Antagonists: 2,6-Dimethyl-3,5-dicarbomethoxy-4-(unsubstituted, 3-methyl-, 4-methyl-, 3-nitro-, 4-nitro-, and 2,4-dinitrophenyl)-1,4-dihydropyridine
    • Fossheim, R.; Svarteng, K.; Mostad, A.; Romming, C.; Shefter, E.; Triggle, D. J. Crystal Structures and Pharmacological Activity of Calcium Channel Antagonists: 2,6-Dimethyl-3,5-dicarbomethoxy-4-(unsubstituted, 3-methyl-, 4-methyl-, 3-nitro-, 4-nitro-, and 2,4-dinitrophenyl)-1,4-dihydropyridine. J. Med. Chem. 1982, 25, 126–131.
    • (1982) J. Med. Chem. , vol.25 , pp. 126-131
    • Fossheim, R.1    Svarteng, K.2    Mostad, A.3    Romming, C.4    Shefter, E.5    Triggle, D.J.6
  • 39
    • 0023696172 scopus 로고
    • Qualitative and quantitative structure-activity relationships for calcium channel modulating 1,4-dihydropyridine derivatives: a hypothetical molecular receptor model
    • Höltje, H. D.; Marrer, S. Qualitative and quantitative structure-activity relationships for calcium channel modulating 1,4-dihydropyridine derivatives: a hypothetical molecular receptor model. Quant. Struct.-Act. Rel. 1988, 7, 174–8.
    • (1988) Quant. Struct.-Act. Rel. , vol.7 , pp. 174-178
    • Höltje, H.D.1    Marrer, S.2
  • 40
    • 0026095516 scopus 로고
    • Active Conformation of 1,4-Dihydropyridine Calcium Entry Blockers. Effect of Size of 2-Aryl Substituent on Rotameric Equilibria and Receptor Binding
    • Rovnyak, G.; Andersen, N.; Gougoutas, J.; Hedberg, A.; Kimball, S. D.; Malley, M.; Moreland, S.; Porubcan, M.; Pudzianowski, A. Active Conformation of 1,4-Dihydropyridine Calcium Entry Blockers. Effect of Size of 2-Aryl Substituent on Rotameric Equilibria and Receptor Binding. J. Med. Chem. 1991, 34, 2521–2524.
    • (1991) J. Med. Chem. , vol.34 , pp. 2521-2524
    • Rovnyak, G.1    Andersen, N.2    Gougoutas, J.3    Hedberg, A.4    Kimball, S.D.5    Malley, M.6    Moreland, S.7    Porubcan, M.8    Pudzianowski, A.9
  • 41
    • 0024536611 scopus 로고
    • Pharmacologic Effects of Wy 27569: A Combined Calcium Channel Blocker And Thromboxane Synthetase Inhibitor
    • Ennis, C.; Granger, S. E.; Middlefell, V. C.; Philpot, M. E.; Shepperson, N. B. Pharmacologic Effects of Wy 27569: A Combined Calcium Channel Blocker And Thromboxane Synthetase Inhibitor. J. Cardiovasc. Pharmacol. 1989, 13, 511–519.
    • (1989) J. Cardiovasc. Pharmacol. , vol.13 , pp. 511-519
    • Ennis, C.1    Granger, S.E.2    Middlefell, V.C.3    Philpot, M.E.4    Shepperson, N.B.5
  • 42
    • 0022393373 scopus 로고
    • Selective Thromboxane Synthetase Inhibitors. 1-[(Aryloxy)alkyl]-1H-imidazoles
    • Cross, P. E.; Dickinson, R. P.; Parry, M. J.; Randall, M. J. Selective Thromboxane Synthetase Inhibitors. 1-[(Aryloxy)alkyl]-1H-imidazoles. J. Med. Chem. 1985, 28, 1427–1432.
    • (1985) J. Med. Chem. , vol.28 , pp. 1427-1432
    • Cross, P.E.1    Dickinson, R.P.2    Parry, M.J.3    Randall, M.J.4
  • 43
    • 0025390935 scopus 로고
    • MOPAC: A semiempirical molecular orbital program
    • Stewart, J. J. MOPAC: A semiempirical molecular orbital program. J. Comp.-Aided Mol. Des. 1990, 4, 1–105.
    • (1990) J. Comp.-Aided Mol. Des. , vol.4 , pp. 1-105
    • Stewart, J.J.1
  • 46
    • 0021325075 scopus 로고
    • Differential Effects of Dazoxiben, a Selective Thromboxane-Synthase Inhibitor, on Platelet and Renal Prostaglandin-Endoperoxide Metabolism
    • Patrignani, P.; Filabozzi, P.; Catella, F.; Pugliese, F.; Patrono, C. Differential Effects of Dazoxiben, a Selective Thromboxane-Synthase Inhibitor, on Platelet and Renal Prostaglandin-Endoperoxide Metabolism. J. Pharmacol. Exp. Ther. 1984, 228(2), 472–477.
    • (1984) J. Pharmacol. Exp. Ther. , vol.228 , Issue.2 , pp. 472-477
    • Patrignani, P.1    Filabozzi, P.2    Catella, F.3    Pugliese, F.4    Patrono, C.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.